US4526963A - Dioxazine pigments - Google Patents
Dioxazine pigments Download PDFInfo
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- US4526963A US4526963A US06/437,369 US43736982A US4526963A US 4526963 A US4526963 A US 4526963A US 43736982 A US43736982 A US 43736982A US 4526963 A US4526963 A US 4526963A
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- 239000000049 pigment Substances 0.000 title abstract description 10
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 title description 4
- 150000005125 dioxazines Chemical class 0.000 claims abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 150000007524 organic acids Chemical class 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
- VIYDSMMKCIILTI-UHFFFAOYSA-N 4,5-dichlorodioxazine Chemical compound ClC1=COON=C1Cl VIYDSMMKCIILTI-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 101150108015 STR6 gene Proteins 0.000 claims 1
- -1 dioxazine compound Chemical class 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000000485 pigmenting effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- INGSGLOWUZARPW-UHFFFAOYSA-N 4-chlorodioxazine Chemical compound ClC1=NOOC=C1 INGSGLOWUZARPW-UHFFFAOYSA-N 0.000 description 1
- KJCWVKRTYSMRBA-UHFFFAOYSA-N 9-butylcarbazol-3-amine Chemical compound NC1=CC=C2N(CCCC)C3=CC=CC=C3C2=C1 KJCWVKRTYSMRBA-UHFFFAOYSA-N 0.000 description 1
- AIMXMLCYGWOKDI-UHFFFAOYSA-N 9-methylcarbazol-3-amine Chemical compound NC1=CC=C2N(C)C3=CC=CC=C3C2=C1 AIMXMLCYGWOKDI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
Definitions
- the present invention relates to dioxazine compounds.
- the invention provides dioxazine compounds of formula I ##STR2## in which each R, independently, is C 1-4 alkyl.
- each R is methyl or ethyl.
- Preferred compounds of formula I are those wherein the groups R are identical.
- the present invention further provides a process for the production of the dioxazine compounds of formula I comprising cyclising a compound of formula II ##STR3## in the presence of an organic acid.
- Preferred organic acids include monocarboxylic acids, e.g. acetic acid, propionic acid or benzoic acid, dicarboxylic acids, e.g. oxalic acid, phthalic acid or terephthalic acid, or sulphonic acids e.g. benzenesulphonic acid or toluenesulphonic acid, or mixtures thereof.
- a particularly preferred acid is p-toluenesulphonic acid.
- the cyclisation of compounds of formula II with elimination of two mols of HCl is suitably carried out by heating at a temperature above 160° C. in the presence of an organic acid and in an inert solvent having a boiling point above 160° C. e.g. chlorobenzenes or nitrobenzene.
- the cyclisation reaction of compounds of formula II leads to a mixture of dioxazine compounds of formula I and chlorinated analogs, i.e. monochlorodioxazine and dichlorodioxazine of formula III ##STR4## wherein n is 0 or 1.
- the organic acid is used in molar excess; the amount of the final compound of formula I depending on the amount of acid employed.
- the reaction of 1 mol of a compound of formula II with 1.5 mols of an acid, e.g. p-toluenesulphonic acid gives a dioxazine mixture which has a chlorine content of 4.5% and contains about 60% of the compound of formula I.
- the dioxazine compounds of formula I are obtained with a yield of 75%.
- the mixture of compounds of formula I with mono- and dichloro-dioxazines form also part of the invention.
- the weight ratio of unchlorinated to chlorinated dioxazines may vary within a large range.
- the compound or compounds of formula I constitute at least 20%, preferably 40 to 90%, more preferably 50 to 80% by weight, of such a mixture.
- the resulting mixture of unchlorinated and chlorinated dioxazines is preferably used as such for technical reasons and since the valuable properties of the dioxazines of formula I as pigments are not negatively affected by the presence of the chlorinated analogs which are also useful as pigments.
- the compounds of formula II used as starting materials are known and may be prepared in accordance with known methods from available compounds.
- the compounds of formula I are useful pigments, e.g. for the mass pigmenting of synthetic plastics and resins, free from or containing solvents, e.g. polyvinyl chloride, of surface coatings, such as paints, whether oil or water based, lacquers and inks. They may also be used in pigment printing, textile coating and for pigmenting paper in the mass. They may be employed for such uses in conventional manner and in conventional amounts.
- the pigments of formula I have good rheological properties.
- the pigmentations obtained employing the compounds of formula I possess notably good fastness properties.
- the coatings and prints obtained with paints, lacquers and inks containing the compounds of formula I are characterized by their brilliance.
- the pigments of formula I or the resulting mixture are preferably post-treated according to known methods, e.g. they may be ground in the presence of salt or in a sand or ball mill.
- the compounds of formula I may also be sulphonated according to known methods and be used in sulphonated form as direct dyes.
- the dispersion obtained is sprayed on aluminium sheet, the spray coating allowed to dry in the air for 30 minutes and then stoved for 30 minutes at 120°. A violet film with very good light and weathering fastness is obtained.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paints Or Removers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Disclosed are dioxazine compounds of formula I ##STR1## in which each R, independently, is C1-4 alkyl, their production and use as pigments.
Description
The present invention relates to dioxazine compounds.
The invention provides dioxazine compounds of formula I ##STR2## in which each R, independently, is C1-4 alkyl.
In formula I the C1-4 alkyl groups as R may be straight-chain or branched. Preferably each R is methyl or ethyl.
Preferred compounds of formula I are those wherein the groups R are identical.
The present invention further provides a process for the production of the dioxazine compounds of formula I comprising cyclising a compound of formula II ##STR3## in the presence of an organic acid.
Preferred organic acids include monocarboxylic acids, e.g. acetic acid, propionic acid or benzoic acid, dicarboxylic acids, e.g. oxalic acid, phthalic acid or terephthalic acid, or sulphonic acids e.g. benzenesulphonic acid or toluenesulphonic acid, or mixtures thereof. A particularly preferred acid is p-toluenesulphonic acid.
The cyclisation of compounds of formula II with elimination of two mols of HCl is suitably carried out by heating at a temperature above 160° C. in the presence of an organic acid and in an inert solvent having a boiling point above 160° C. e.g. chlorobenzenes or nitrobenzene. In general, the cyclisation reaction of compounds of formula II leads to a mixture of dioxazine compounds of formula I and chlorinated analogs, i.e. monochlorodioxazine and dichlorodioxazine of formula III ##STR4## wherein n is 0 or 1.
Preferably the organic acid is used in molar excess; the amount of the final compound of formula I depending on the amount of acid employed. For example, the reaction of 1 mol of a compound of formula II with 1.5 mols of an acid, e.g. p-toluenesulphonic acid, gives a dioxazine mixture which has a chlorine content of 4.5% and contains about 60% of the compound of formula I. When reacting 1 mol of a compound of formula II with 2.5 mols of the same acid, the dioxazine compounds of formula I are obtained with a yield of 75%.
The mixture of compounds of formula I with mono- and dichloro-dioxazines form also part of the invention. The weight ratio of unchlorinated to chlorinated dioxazines may vary within a large range. Suitably the compound or compounds of formula I constitute at least 20%, preferably 40 to 90%, more preferably 50 to 80% by weight, of such a mixture.
The resulting mixture of unchlorinated and chlorinated dioxazines is preferably used as such for technical reasons and since the valuable properties of the dioxazines of formula I as pigments are not negatively affected by the presence of the chlorinated analogs which are also useful as pigments.
The compounds of formula II used as starting materials are known and may be prepared in accordance with known methods from available compounds.
The compounds of formula I, whether in pure form or in form of a mixture with chlorinated dioxazines as stated above, are useful pigments, e.g. for the mass pigmenting of synthetic plastics and resins, free from or containing solvents, e.g. polyvinyl chloride, of surface coatings, such as paints, whether oil or water based, lacquers and inks. They may also be used in pigment printing, textile coating and for pigmenting paper in the mass. They may be employed for such uses in conventional manner and in conventional amounts.
The pigments of formula I have good rheological properties. The pigmentations obtained employing the compounds of formula I possess notably good fastness properties. Furthermore, the coatings and prints obtained with paints, lacquers and inks containing the compounds of formula I are characterized by their brilliance.
After synthesis and before use, the pigments of formula I or the resulting mixture are preferably post-treated according to known methods, e.g. they may be ground in the presence of salt or in a sand or ball mill.
The compounds of formula I may also be sulphonated according to known methods and be used in sulphonated form as direct dyes.
The following Examples illustrate the invention. All temperatures are in degrees Centigrade and parts and percentages are by weight unless stated to the contrary.
(a) 157.5 g 3-amino-N-ethyl-carbazol and 0.75 g FeCl3 (powd.) are mixed with 750 ml o-dichlorobenzene and the resulting mixture is heated to 70°. While stirring 24 g 2,3,5,6-tetrachloro-benzoquinone and 16.5 g sodium bicarbonate are added alternately and portionwise, over the course of 5 hours and stirring is continued for a further 2 hour period. The mixture is cooled overnight and about 50 ml o-dichlorobenzene are then distilled off at 80°-85° under reduced pressure. 80 g p-toluene sulphonic acid are added to the mixture and the whole is stirred at 80°-85° for about 15 minutes.
(b) 200 ml o-dichlorobenzene are heated to 180°, the heating being adjusted in such a way that a small amount of o-dichlorobenzene is continuously distilled off, and a light stream of nitrogen is introduced into the reaction flask. The suspension obtained under (a) is added slowly with stirring at a temperature between 175° and 180° to the boiling o-dichlorobenzene. During the addition, about 350 ml o-dichlorobenzene are distilled off. The flask containing the suspension (a) is finally rinsed with 100-150 ml o-dichlorobenzene. For the completion of the reaction, the mixture is further refluxed at 175°-180° for 6 hours. After cooling to 120°, the reaction mixture is saturated with gaseous ammonia. The resulting dioxazine mixture is precipitated, filtered off, successively washed with about 600 ml o-dichlorobenzene heated to 120°, 1250 ml cold methanol and about 1500 ml water and dried in vacuo at 120°. There is obtained a mixture of dioxazines having a 4,5% chlorine content and containing about 60% of the dioxazine of formula ##STR5## and 40% of a mixture of the mono- and dichloro-equivalents.
By following the procedure of Example 1 but using 64 g terephthalic acid instead of p-toluenesulphonic acid, there is obtained a mixture having a 4.0% chlorine content and the same properties as the compound of Example 1.
By following the procedure of Example 1 but replacing the 157.5 g 3-amino-N-ethyl-carbazol by equimolar amounts of
(a) 3-amino-N-methylcarbazol, or
(b) 3-amino-N-butylcarbazol
a mixture of pigments having the same colouring properties as the compound of Example 1, is obtained.
Four parts of the pigment of Example 1 are added to 96 parts of a mixture of
50 parts of a 60% solution of coco aldehyde-melamine resin of 32% fat content in xylene,
30 parts of a 50% melamine resin solution in butanol,
10 parts of xylene and
10 parts of ethylene glycol monoethylether
and the mixture ground for 24 hours in a ball mill. The dispersion obtained is sprayed on aluminium sheet, the spray coating allowed to dry in the air for 30 minutes and then stoved for 30 minutes at 120°. A violet film with very good light and weathering fastness is obtained.
Claims (17)
1. A mixture of dioxazine compounds consisting essentially of a compound or mixture of compounds of formula I ##STR6## in which each R, independently, is C1-4 alkyl, in an amount at least 20%, by weight, and a monochloro and a dichloro-dioxazine of formula III ##STR7## wherein each R is as defined above and n is 0 or 1.
2. A mixture according to claim 1 wherein each R is methyl or ethyl.
3. A mixture according to claim 1 comprising 40 to 90%, by weight, of a compound or mixture of compounds of formula I.
4. A mixture according to claim 3 comprising 50 to 80%, by weight, of a compound or mixture of compounds of formula I.
5. A mixture according to claim 3 consisting essentially of about 60%, by weight, of a compound of formula I in which each R is ethyl and 40% of a mixture of compounds of formula III in which each R is ethyl.
6. A mixture according to claim 3 wherein each R is methyl or ethyl.
7. A process for producing a dioxazine compound of formula I ##STR8## in which each R, independently, is C1-4 alkyl, which comprises cyclizing a compound of formula II ##STR9## in which each R is as defined above, in the presence of an organic acid.
8. A process according to claim 7 wherein the organic acid is a monocarboxylic acid, a dicarboxylic acid, a sulphonic acid or a mixture thereof.
9. A process according to claim 7, wherein the acid is a sulphonic acid or a mixture thereof.
10. A process according to claim 8 wherein the organic acid is acetic, propionic, benzoic, oxalic, phthalic, terephthalic, benzenesulphonic or toluenesulphonic acid or a mixture thereof.
11. A process according to claim 7 wherein the organic acid is present in a molar excess with respect to the compound of formula II.
12. A process according to claim 8 wherein the organic acid is present in a molar excess with respect to the compound of formula II.
13. A process according to claim 10 wherein the organic acid is present in a molar excess with respect to the compound of formula II.
14. A process according to claim 7 wherein the cyclization is effected at a temperature above 160° C. in an inert solvent having a boiling point above 160° C.
15. A process according to claim 10 wherein the cyclization is effected at a temperature above 160° C. in an inert solvent having a boiling point above 160° C.
16. A process according to claim 11 wherein the cyclization is effected at a temperature above 160° C. in an inert solvent having a boiling point above 160° C.
17. A process according to claim 13 wherein the cyclization is effected at a temperature above 160° C. in an inert solvent having a boiling point above 160° C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3143403 | 1981-11-02 | ||
| DE3143403 | 1981-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4526963A true US4526963A (en) | 1985-07-02 |
Family
ID=6145391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/437,369 Expired - Lifetime US4526963A (en) | 1981-11-02 | 1982-10-28 | Dioxazine pigments |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4526963A (en) |
| JP (1) | JPS5884857A (en) |
| CH (1) | CH656139A5 (en) |
| FR (1) | FR2515668A1 (en) |
| GB (1) | GB2108995B (en) |
| HK (1) | HK53288A (en) |
| IT (1) | IT1189406B (en) |
| SG (1) | SG14888G (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4751300A (en) * | 1986-02-19 | 1988-06-14 | Sumitomo Chemical Company, Limited | Production of dioxazine compound |
| US5734050A (en) * | 1994-05-30 | 1998-03-31 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| US6255482B1 (en) * | 1997-10-24 | 2001-07-03 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| US6359131B1 (en) | 1999-03-25 | 2002-03-19 | Clariant Gmbh | Process for preparing dioxazine compounds |
| US6617453B1 (en) | 1997-10-24 | 2003-09-09 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| US20040063889A1 (en) * | 2001-02-21 | 2004-04-01 | Kaul Bansi Lal | Copolymer composition having pigment like properties |
| US20080156230A1 (en) * | 2005-02-25 | 2008-07-03 | Heino Heckmann | Method for Producing Transparent Dioxazine Pigments |
| US20100196816A1 (en) * | 2007-07-05 | 2010-08-05 | Clariant Finance (Bvi) Limited | Pigment Preparations Based on Dioxazines |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0848687A (en) * | 1994-05-30 | 1996-02-20 | Nippon Kayaku Co Ltd | Production of dioxazine compound, coloring material and plate-like crystal |
| JP4687186B2 (en) * | 2005-03-29 | 2011-05-25 | Ｄｉｃ株式会社 | Dioxazine violet pigment composition |
| US20110098466A1 (en) * | 2007-08-31 | 2011-04-28 | Clariant Finance (Bvi) Limited | Synthesis Of Triphenodioxazine Pigments |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2026092A (en) * | 1928-06-06 | 1935-12-31 | Gen Aniline Works Inc | Dyestuffs of the oxazine series and process of preparing them |
| US3912732A (en) * | 1972-05-09 | 1975-10-14 | Ciba Geigy Corp | Dioxazine dyestuffs |
| US4400504A (en) * | 1980-12-02 | 1983-08-23 | Bayer Aktiengesellschaft | Dioxazine reactive dyestuffs |
| US4459233A (en) * | 1981-04-13 | 1984-07-10 | Basf Aktiengesellschaft | Purification of crude organic pigments |
-
1982
- 1982-10-20 FR FR8217669A patent/FR2515668A1/en active Granted
- 1982-10-21 CH CH6123/82A patent/CH656139A5/en not_active IP Right Cessation
- 1982-10-28 US US06/437,369 patent/US4526963A/en not_active Expired - Lifetime
- 1982-10-29 IT IT49399/82A patent/IT1189406B/en active
- 1982-10-29 GB GB08231011A patent/GB2108995B/en not_active Expired
- 1982-11-01 JP JP57190910A patent/JPS5884857A/en active Granted
-
1988
- 1988-03-02 SG SG148/88A patent/SG14888G/en unknown
- 1988-07-14 HK HK532/88A patent/HK53288A/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2026092A (en) * | 1928-06-06 | 1935-12-31 | Gen Aniline Works Inc | Dyestuffs of the oxazine series and process of preparing them |
| US3912732A (en) * | 1972-05-09 | 1975-10-14 | Ciba Geigy Corp | Dioxazine dyestuffs |
| US4400504A (en) * | 1980-12-02 | 1983-08-23 | Bayer Aktiengesellschaft | Dioxazine reactive dyestuffs |
| US4459233A (en) * | 1981-04-13 | 1984-07-10 | Basf Aktiengesellschaft | Purification of crude organic pigments |
Non-Patent Citations (2)
| Title |
|---|
| Venkataraman, The Chemistry of Synthetic Dyes, vol. V, Academic Press, New York, (1971), pp. 419 427. * |
| Venkataraman, The Chemistry of Synthetic Dyes, vol. V, Academic Press, New York, (1971), pp. 419-427. |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4751300A (en) * | 1986-02-19 | 1988-06-14 | Sumitomo Chemical Company, Limited | Production of dioxazine compound |
| US5734050A (en) * | 1994-05-30 | 1998-03-31 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| US5859242A (en) * | 1994-05-30 | 1999-01-12 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| US6255482B1 (en) * | 1997-10-24 | 2001-07-03 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| US6355795B1 (en) | 1997-10-24 | 2002-03-12 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| US6617453B1 (en) | 1997-10-24 | 2003-09-09 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| US6359131B1 (en) | 1999-03-25 | 2002-03-19 | Clariant Gmbh | Process for preparing dioxazine compounds |
| US20040063889A1 (en) * | 2001-02-21 | 2004-04-01 | Kaul Bansi Lal | Copolymer composition having pigment like properties |
| US7087677B2 (en) | 2001-02-21 | 2006-08-08 | Mitchell A. Winnik | Copolymer composition having pigment like properties |
| US20080156230A1 (en) * | 2005-02-25 | 2008-07-03 | Heino Heckmann | Method for Producing Transparent Dioxazine Pigments |
| US20100196816A1 (en) * | 2007-07-05 | 2010-08-05 | Clariant Finance (Bvi) Limited | Pigment Preparations Based on Dioxazines |
| US8293441B2 (en) | 2007-07-05 | 2012-10-23 | Clariant Finance (Bvi) Limited | Pigment preparations based on dioxazines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2108995B (en) | 1985-03-06 |
| FR2515668A1 (en) | 1983-05-06 |
| HK53288A (en) | 1988-07-22 |
| JPS5884857A (en) | 1983-05-21 |
| JPH0435506B2 (en) | 1992-06-11 |
| CH656139A5 (en) | 1986-06-13 |
| IT1189406B (en) | 1988-02-04 |
| SG14888G (en) | 1988-07-08 |
| IT8249399A0 (en) | 1982-10-29 |
| FR2515668B1 (en) | 1985-01-11 |
| GB2108995A (en) | 1983-05-25 |
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